Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/60—Sugars; Derivatives thereof
  • A61K8/602—Glycosides, e.g. rutin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/005—Preparations for sensitive skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
  • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
  • Y10S516/914—The agent contains organic compound containing nitrogen, except if present solely as NH4+
  • Y10S516/915—The compound contains -C[=O]NHH where substitution may be made for the hydrogen

Definitions

• the present invention relates to novel active compounds, their preparation and their use in the field of cosmetic and of pharmaceutical dermatology.
• the present invention relates to active compounds and cosmetic and dermatological preparations comprising such active compound combinations.
• the present invention relates to active compounds which have surfactant properties.
• the invention further relates to cosmetic and dermatological preparations which contain such substances.
• the present invention relates to cosmetic cleansing agents.
• Agents of this type are known per se. In this context, they are essentially surface-active substances or substance mixtures which are offered to the consumer in various preparations.
• Preparations of this type are, for example, bubble baths and shower baths, solid and liquid soaps or so-called “syndets” (synthetic detergents), shampoos, hand-washing pastes, intimate cleansing agents, special cleansing agents for infants and the like.
• solid and liquid soaps solid and liquid soaps or so-called “syndets” (synthetic detergents), shampoos, hand-washing pastes, intimate cleansing agents, special cleansing agents for infants and the like.
• Cosmetic emulsions also contain interfacially active substances, so-called emulsifiers. These reduce the surfaces of contact between the phases and form oil/water interfacial films on the phase boundary. As a result, the irreversible confluence of the dispersed phase is counteracted.
• Efficient emulsifiers are therefore distinguished by a very good emulsifying, solubilizing and dispersing ability. To a great extent, it is desirable that such substances do not cause skin irritation.
• the choice of such substances known to the prior art is restricted. it was therefore an object of the present invention to enrich the prior art in this respect.
• Preparations of this type are known per se. In this context, they are essentially surface-active substances or substance mixtures which are offered to the consumer in various preparations. Preparations of such a type are in general distinguished by a high water content to a greater or lesser degree, but can also be present, for example, as a concentrate.
• preparations which are intended for the shower bath do not differ or hardly differ from bath preparations apart from the fact that in the case of shower preparations products of higher viscosity are preferred, which do not run from the hand after removal from the container. In the case of bath preparations, this is less of practical importance.
• preparations of various types it being possible to vary the properties of the fat or oil phase by addition of surface-active substances.
• preparations can be formulated which either produce spreading oil films, oil-in-water systems or even total solubilizates on the bath-water surface.
• Foaming formulations but also only slightly foaming or non-foaming formulations, are possible.
• the functionality of preparations of this type is restricted in oil bath or oil cream bath preparations to the refatting or superfatting of the uppermost layers of skin.
• the present invention relates to cosmetic and dermatological preparations for the prophylaxis and treatment of cosmetic or dermatological cell changes, in particular skin changes such as, for example, skin ageing, in particular the cell ageing caused by oxidative processes, in particular skin ageing.
• alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids of the general formula ##STR1## where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, and their salts, and a process for the preparation of alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids of the general formula ##STR2## where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, and their salts, characterized in that
• reaction product thus obtained is purified by dialysis, preferably electrodialysis,
• alkyl 2-acetamido-2-deoxy-D-glucopyranaside uronic acids of the general formula ##STR3## where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, as surface-active and/or interfacially active active compounds, in particular as detergent surfactants or emulsifiers, and where the uronic acids can preferably be present in the form of their salts, in particular as alkali metal salts, of these preferably the sodium salt, or as ammonium, alkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium salts.
• Mixtures of ⁇ - and ⁇ -glycosides can also be advantageous according to the invention.
• a plethora of processes which are able to separate the anomers are known to the person skilled in the art, for example chromatographic processes.
• alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids and their advantageous salts according to the invention are derived formally as well as practically from chitin, which is characterized by the structural formula ##STR4##
• chitin derivatives namely of chitosan, a hydrolysis product of chitin
• chitin for example, is better suited than the chitin on which it is based, as a thickener or stabilizer and improves the adhesion and water-resistance of polymeric films. Representing a multiplicity of places where this is found in the prior art: H. P. Fiedler, "Lexikon der Hilfstoffe fur Pharmazie, Kosmetik und angrenzende füre" [Encyclopedia of auxiliaries for pharmacy, cosmetics and neighbouring fields], 4th Edition 1989, Editio Cantor, Aulendorf, p. 349, headword "Chitosan”.
• the ground chitin is treated in the presence of heat, advantageously at temperatures of 40-70° C., in particular about 55° C., with acid and a first aliphatic alcohol.
• a suitable temperature range for this reaction step and for the distillative removal of the first aliphatic alcohol is between 80 and 100° C., preferably about 90° C.
• the acid catalysis can be carried out on acidic ion-exchange resins, e.g. Amberlite IR 120, by means of camphorsulphonic acid or hydrochloric acid.
• acidic ion-exchange resins e.g. Amberlite IR 120
• camphorsulphonic acid or hydrochloric acid e.g. camphorsulphonic acid or hydrochloric acid.
• a neutralisation can advantageously be carried out, e.g. using sodium hydroxide solution or on basic ion-exchange resins.
• an anomer mixture is obtainable which can be separated into the anomers by methods familiar to the person skilled in the art.
• the ⁇ -anomer is obtained, usually in a nine-fold excess compared with the ⁇ -anomer.
• alkyl 2-acetamido-2-deoxyglucopyranosides which are known per se are also outstandingly suitable as surface-active or interfacially active substances. Therefore, also according to the invention is the use of alkyl 2-acetamido-2-deoxyglucopyranosides of the general structural formula ##STR7## where R is representative of the group consisting of branched and unbranched alkyl of 1-48 C atoms, in particular of 14-22, preferably 16-18, C atoms, as surface-active and/or interfacially active active compounds, in particular as detergent surfactants or emulsifiers.
• the cosmetic or dermatological formulations according to the invention can be made up in the customary manner and used for the treatment, the care and the cleansing of the skin and/or the hair and as a make-up product in decorative cosmetics. They preferably contain 0.001% by weight to 10% by weight, but in particular 0.01% by weight to 6% by weight, based on the total weight of the composition, of the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention.
• the cosmetic and dermatological preparations according to the invention are applied to the skin and/or the hair in adequate amounts in the manner customary for cosmetics.
• Cosmetic and dermatological preparations according to the invention can be present in various forms.
• alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention to aqueous systems or surfactant preparations for cleansing the skin and the hair.
• the cosmetic and dermatological preparations according to the invention can contain cosmetic auxiliaries, such as are customarily used in such preparations, e.g. preservatives, bactericides, perfumes, substances for preventing foaming, colourants, pigments which have a colouring action, thickening agents, surface-active substances, emulsifiers, emollient, moisturizing and/or moisture-retaining substances, fats, oils, waxes or other customary constituents of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
• cosmetic auxiliaries such as are customarily used in such preparations, e.g. preservatives, bactericides, perfumes, substances for preventing foaming, colourants, pigments which have a colouring action, thickening agents, surface-active substances, emulsifiers, emollient, moisturizing and/or moisture-retaining substances, fats, oils, waxes or other
• alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids can also be combined with antioxidants.
• convenient antioxidants which can be used are all antioxidants suitable or customary for cosmetic and/or dermatological applications.
• the antioxidants are selected from the group consisting of amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocaninic acid) and their derivatives, peptides such as D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g.
• amino acids e.g. glycine, histidine, tyrosine, tryptophan
• imidazoles e.g. urocaninic acid
• peptides such as D,L-carnosine, D-carnosine, L-carnosine and their derivatives (e.g. anserine)
• thiols e.g. thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters
• salts dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and its derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulphoximine compounds (e.g.
• buthionine sulphoximine in very low tolerable doses (e.g. pmol to ⁇ mol/kg), furthermore (metal) chelators (e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), ⁇ -hydroxy acids (e.g. citric acid, lactic acid, maleic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (e.g.
• metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
• ⁇ -hydroxy acids e.g. citric acid, lactic acid, maleic acid
• humic acid bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their
• ⁇ -linolenic acid linoleic acid, oleic acid
• folic acid and its derivatives ubiquinone and ubiquinol and their derivatives
• vitamin C and derivatives e.g. ascorbyl palmitate, Mg-ascorbyl phosphate, ascorbyl acetate
• tocopherols and derivatives e.g.
• vitamin E acetate
• vitamin A and derivatives vitamin A palmitate
• coniferyl benzoate of benzoin rutic acid and its derivatives, ⁇ -glycosylrutin, ferulic acid, furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, nordihydroguairetic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (e.g. ZnO, ZnSO 4 ), selenium and its derivatives (e.g. selenomethionine), stilbenes and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) and the suitable derivatives according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these mentioned active compounds.
• the amount of the abovementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 300% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the preparation.
• vitamin E and/or its derivatives are the antioxidant(s), it is advantageous to select their respective concentrations from the range from 0.001-10% by weight, based on the total weight of the formulation.
• vitamin A, or vitamin A derivatives, or carotenes or their derivatives are the antioxidant(s) it is advantageous to select their respective concentrations from the range from 0.001-100% by weight, based on the total weight of the formulation.
• Emulsions according to the invention are advantageous and contain, for example, the fats, oils, waxes and other fatty materials mentioned, as well as water and an emulsifier, such as is customarily used for such a type of formulation.
• oils such as triglycerides of capric or of caprylic acid, but preferably castor oil;
• esters of fatty acids with alcohols of low C number e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
• silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes as well as mixed forms thereof;
• saturated compounds such as hydrocarbons of natural or synthetic origin (petroleum jelly, squalane).
• the aqueous phase of the preparations according to the invention if desired advantageously contains alcohols, diols or polyols of low C number, as well as their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products and also, in particular, one or more thickening agents, which can advantageously be selected from the group consisting of silica, aluminium silicates, polysaccharides and their derivatives, e.g.
• hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose particularly advantageously from the group consisting of the polyacrylates, preferably a polyacrylate from the group consisting of the so-called carbopols, for example carbopols of the types 980, 981, 1382, 2984, 5984, in each case individually or in combination.
• mixtures of the abovementioned solvents are used.
• water can be a further constituent.
• Gels according to the invention customarily contain alcohols of low C number, e.g. ethanol, isopropanol, 1,2-propanediol, glycerol and water or an above-mentioned oil in the presence of a thickening agent which in the case of oily-alcoholic gels is preferably silica or an aluminium silicate, and in the case of aqueous-alcoholic or alcoholic gels preferably a polyacrylate.
• alcohols of low C number e.g. ethanol, isopropanol, 1,2-propanediol, glycerol and water or an above-mentioned oil
• a thickening agent which in the case of oily-alcoholic gels is preferably silica or an aluminium silicate, and in the case of aqueous-alcoholic or alcoholic gels preferably a polyacrylate.
• Suitable propellants for preparations according to the invention which can be sprayed from aerosol containers are the customary known easily volatile, liquefied propellants, for example hydrocarbons (propane, butane, isobutane), which can be employed on their own or as a mixture with one another. Compressed air can also advantageously be used.
• preparations according to the invention can additionally contain substances which absorb UV radiation in the UVB range, the total amount of the filter substances being, for example, 0.1% by weight to 30% by weight, preferably 0.5 to 10% by weight, in particular 1.0 to 6.0% by weight, based on the total weight of the preparations, in order to make available cosmetic preparations which protect the hair or the skin from the entire range of ultraviolet radiation. They can also be used as sunscreens for the hair or the skin.
• UVB filter substances these can be oil-soluble or water-soluble.
• Advantageous oil-soluble UVB filters according to the invention are, for example:
• 3-benzylidencamphor derivatives preferably 3-(4-methylbenzylidene)camphor, 3-benzylidenecamphor;
• 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4-dimethylaminobenzoate, amyl 4-dimethylaminobenzoate;
• esters of cinnamic acid preferably 2-ethylhexyl 4-methoxycinnamate, isopentyl 4-methoxycinnamate;
• esters of salicylic acid preferably 2-ethylhexyl salicylate, 4-isopropylbenzyl salicylate, homomenthyl salicylate;
• benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
• esters of benzylidenemalonic acid preferably di(2-ethylhexyl) 4-methyoxybenzylidenemalonate, 2,4,6-trianilino-(p-carbo-2'-ethyl-1'-hexyloxy)-1,3,5-triazine.
• Advantageous water-soluble UVB filters are, for example:
• 2-phenylbenzimidazole-5-sulphonic acid such as its sodium, potassium or its triethanolammonium salt, as well as the sulphonic acid itself;
• sulphonic acid derivatives of benzophenone preferably 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid and its salts
• sulphonic acid derivatives of 3-benzylidenecamphor such as, for example, 4-(2-oxo-3-bornylidenemethyl)-benzenesulphonic acid, 2-methyl-5-(2-oxo-3-bornylidenemethyl)sulphonic acid and their salts.
• UVB filters which can be used in combination with the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention, should of course be non-limiting.
• the invention also relates to the use of a combination of the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention with at least one UVB filter as antioxidant or the use of a combination of the tocopherylglycosides according to the invention with at least one UVB filter as antioxidant in a cosmetic or dermatological preparation.
• alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention with UVA filters which to date are customarily contained in cosmetic preparations.
• These substances are preferably derivatives of dibenzoylmethane, in particular 1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)propane-1,3-dione and 1-phenyl-3-(4'-isopropylphenyl)propane-1,3-dione.
• These combinations and preparations which contain these combinations are also a subject of the invention.
• the amounts used for the UVB combination can be employed.
• the invention also relates to the use of a combination of the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention with at least one UVA filter as antioxidant or the use of a combination of the tocopherylgycosides according to the invention with at least one UVA filter as antioxidant in a cosmetic or dermatological preparation.
• the invention also relates to the use of a combination of the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention with at least one UVA filter and at least one UVB filter as antioxidant or the use of a combination of the tocopherylglycosides according to the invention with at least one UVA filter and at least one UVB filter as antioxidant in a cosmetic or dermatological preparation.
• Cosmetic and dermatological preparations having an efficacious content of alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention can also contain inorganic pigments which are customarily used in cosmetics for the protection of the skin from UV rays.
• inorganic pigments which are customarily used in cosmetics for the protection of the skin from UV rays.
• these are oxides of titanium, zinc, iron, zirconium, silicon, manganese, aluminium, cerium and mixtures thereof, as well as modifications in which the oxides are the active agents.
• they are pigments based on titanium dioxide.
• UVA filter and pigment or preparations which contain this combination are also a subject of the invention.
• the amounts mentioned for the above combinations can be used.
• Cosmetic and dermatological preparations for the protection of the hair from UV rays according to the invention are, for example, shampoos, preparations which are applied when rinsing the hair before or after shampooing, before or after permanent wave treatment, or before or after dyeing or bleaching hair, preparations for hot-air drying or setting of the hair, preparations for dyeing or bleaching, a hairdressing and treatment lotion, a hair lacquer or permanent wave compositions.
• the cosmetic and dermatological preparations contain active compounds and auxiliaries, such as are customarily used for this type of preparations for hair care and hair treatment.
• auxiliaries used are preservatives, surface-active substances, substances for preventing foaming, thickening agents, emulsifiers, fats, oils, waxes, organic solvents, bactericides, perfumes, dyes or pigments whose object is to colour the hair or the cosmetic or dermatological preparation itself, electrolytes and substances preventing the hair from becoming greasy.
• Electrolytes within the meaning of the present invention are water-soluble alkali metal, ammonium, alkaline earth metal (including magnesium) and zinc salts of inorganic anions and any desired mixtures of those salts, where it must be guaranteed that these salts are distinguished by pharmaceutical or cosmetic acceptability.
• the anions according to the invention are preferably selected from the group consisting of the chlorides, the sulphates and hydrogen sulphates, the phosphates, hydrogen phosphates and the linear and cyclic oligophosphates as well as the carbonates and hydrogen carbonates.
• Cosmetic preparations which are a skin-cleansing agent or shampoo preferably contain at least one further anionic, non-ionic or amphoteric and surface-active substance or surface-active betaines, or alternatively mixtures of such substances, furthermore alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention in aqueous medium and auxiliaries, such as are customarily used for this purpose.
• the surface-active substance or the mixtures of these substances can be present in a concentration of between 1% by weight and 50% by weight in the shampoo.
• the cosmetic or dermatological preparations are present in the form of a lotion which is rinsed out and is applied, for example, before or after bleaching, before or after shampooing, between two shampooing steps, or before or after permanent wave treatment, they are in this case, for example, aqueous or aqueous-alcoholic solutions which optionally contain surface-active substances whose concentration can be between 0.1 and 10% by weight, preferably between 0.2 and 5% by weight.
• These cosmetic or dermatological preparations can also be aerosols containing the auxiliaries customarily used for this purpose.
• a cosmetic preparation in the form of a lotion which is not rinsed out in particular a lotion for setting the hair, a lotion which is used during hot-air drying of the hair, or a hairdressing and treatment lotion, is in general an aqueous, alcoholic or aqueous-alcoholic solution and contains at least one cationic, anionic, non-ionic or amphoteric polymer or alternatively mixtures thereof, as well as active compound combinations according to the invention in an efficacious concentration.
• the amount of the polymers used is, for example, between 0.1 and 10% by weight, preferably between 0.1 and 3% by weight.
• Cosmetic preparations for the treatment and care of the skin and of the hair which contain alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention can be present as emulsions which are of the non-ionic or cationic type.
• non-ionic emulsions contain oils or fatty alcohols which, for example, can also be polyethoxylated or polypropoxylated, or alternatively mixtures of both organic components.
• These emulsions optionally contain cationic surface-active substances.
• cosmetic preparations for the treatment and care of the hair can also be present as gels which, besides an efficacious content of alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention, preferably contain water, further organic thickening agents, e.g. gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, e.g. aluminium silicates such as, for example, bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
• the thickening agent is contained in the gel, for example, in an amount of between 0.1 and 30% by weight, preferably of between 0.5 and 15% by weight.
• the amount of the alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention in a composition intended for the hair is 0.05% by weight to 10% by weight, in particular 0.5% by weight to 5% by weight, based on the total weight of the composition.
• Aqueous cosmetic cleansing agents according to the invention or cleansing agent concentrates which are low in water or water-free intended for aqueous cleansing can contain anionic, non-ionic and/or amphoteric surfactants, for example conventional soaps, e.g. fatty acid salts of sodium, alkyl sulphates, alkyl ether sulphates, alkane- and alkylbenzenesulphonates, sulphoacetates, sulphobetaines, sarcosinates, amidosulphobetaines, sulphosuccinates, sulphosuccinic acid monoesters, alkyl ether carboxylates, protein-fatty acid condensates, alkylbetaines and amidobetaines, fatty acids alkanolamides and/or polyglycol ether derivatives.
• anionic, non-ionic and/or amphoteric surfactants for example conventional soaps, e.g. fatty acid salts of sodium, alkyl s
• Cosmetic preparations which are cosmetic cleansing preparations for the skin can be present in liquid or solid form.
• these alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids according to the invention or their salts they can preferably contain at least one anionic, non-ionic or amphoteric surface-active substance or mixtures thereof, and if desired one or more electrolytes and auxiliaries, such as are customarily used for this purpose.
• the surface-active substance can be present in a concentration of between 1 and 94% by weight in the cleansing preparations, based on the total weight of the preparations.
• cosmetic preparations which are a shampoo preferably contain at least one anionic, non-ionic or amphoteric surface-active substance or mixtures thereof, and if desired an electrolyte and auxiliary according to the invention, such as are customarily used for this purpose.
• the surface-active substance can be present in a concentration of between 1% by weight and 94% by weight in the shampoo.
• compositions according to the invention contain water and, if desired, the additives customary in cosmetics, for example perfume, thickener, colourants, antimicrobial substances, refatting agents, complexing and sequestering agents, pearl lustre agents, plant extracts, vitamins, active compounds and the like.
• the additives customary in cosmetics for example perfume, thickener, colourants, antimicrobial substances, refatting agents, complexing and sequestering agents, pearl lustre agents, plant extracts, vitamins, active compounds and the like.
• the amount of alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids used according to the invention in these preparations is 0.001% by weight to 10% by weight, in particular 0.1% by weight to 3% by weight, based on the total weight of the preparations.
• the invention also relates to the process for the preparation of the cosmetic compositions according to the invention, which is characterized in that alkyl 2-acetamido-2-deoxy-D-glucopyranoside uronic acids are incorporated into cosmetic and dermatological formulations in a manner known per se.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with stearyl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with cetyl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with decyl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with dodecyl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with tetradecyl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with palmityl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.
• Ground chitin is treated at 55° C. with hydrochloric acid and butyl alcohol and the reaction product thus obtained is purified by electrodialysis.
• the reaction product is reacted with eicosyl alcohol with acid catalysis with camphorsulphonic acid at 90° C. and the butyl alcohol is stripped off under a water-jet vacuum at 90° C.
• the product is neutralized with NaOH and the product is oxidized to the final product at 60° C. using Adam's catalyst.

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• 1996
  • 1996-04-27 DE DE19617019A patent/DE19617019A1/de not_active Ceased
• 1997
  • 1997-04-04 EP EP97105575A patent/EP0808842A3/fr not_active Withdrawn
  • 1997-04-22 JP JP9117410A patent/JPH1067629A/ja active Pending
  • 1997-04-24 US US08/840,002 patent/US6037460A/en not_active Expired - Fee Related
• 1999
  • 1999-12-23 US US09/470,775 patent/US6156326A/en not_active Expired - Fee Related
• 2000
  • 2000-09-12 US US09/660,224 patent/US6387961B1/en not_active Expired - Fee Related

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